Form 4: Procore Chairman Executes Stock Sales and 1.7M Share Collar

Chairman Craig Courtemanche exercised options and sold 56,122 shares while entering a complex hedging transaction on 1.7 million shares for liquidity purposes.

Summary

• Craig F. Courtemanche Jr., Chairman of the Board, exercised stock options for 56,122 shares at a strike price of $2.42 per share on June 10, 2026.
• All 56,122 shares were subsequently sold on the same day at weighted average prices ranging from $44.69 to $45.29, totaling approximately $2.53 million in gross proceeds.
• On June 12, 2026, Courtemanche entered into a revolving loan and collar transaction involving 1,700,000 shares held in family trusts.
• The collar transaction establishes a price floor at $37.5716 (put option) and a price cap at $60.9986 (call option) to provide liquidity while maintaining voting rights.
• Following these transactions, Courtemanche continues to hold over 5.3 million shares directly and indirectly through various trusts.

Sentiment

Score: 6

Explanation: StockSavvy.ai views this as neutral to slightly positive. While the Chairman sold shares, it was a small fraction of his total holdings and driven by expiring options. The collar indicates a long-term horizon through 2029.

Positives

• The reporting person maintains a massive equity stake in the company, with over 5.3 million shares held across direct and indirect accounts.
• The sales were conducted under a pre-arranged Rule 10b5-1 trading plan dated December 9, 2025, which reduces concerns regarding opportunistic timing.
• The collar transaction allows the Chairman to retain voting and dividend rights on 1.7 million shares while securing liquidity.
• The exercise price of $2.42 represents a significant gain compared to the market price of approximately $45.00.

Negatives

• The immediate sale of 100% of the exercised options (56,122 shares) results in no net increase in direct share ownership from that specific grant.
• The implementation of a collar on 1.7 million shares suggests a desire to hedge against significant downside risk below $37.57 per share.

Risks

• If the stock price exceeds $60.9986 in June 2029, the 1.7 million pledged shares may be called away, effectively capping the Chairman's upside on that specific block.
• The use of shares as collateral for a revolving loan introduces potential forced liquidation risk if the terms of the loan agreement are breached.
• Market perception of large-scale hedging by a founder/Chairman can sometimes be interpreted as a lack of confidence in significant near-term price appreciation.

Future Outlook

The Chairman has secured a long-term hedging and liquidity strategy that extends through June 2029. This suggests a commitment to maintaining a large position for at least the next three years while managing personal financial liquidity through structured bank products rather than direct market sales.

Management Comments

• The revolving loan and collar transactions were executed for general liquidity purposes.
• The reporting person generally retains voting and dividend rights over the pledged shares during the term of the pledge.

Industry Context

StockSavvy.ai notes that equity collars are a common sophisticated financial tool used by high-net-worth tech executives to diversify or gain liquidity without triggering immediate massive tax events or losing corporate control. This strategy is frequently seen among founders of companies like Salesforce and ServiceNow.

Comparison to Industry Standards

• The use of a 10b5-1 plan is the gold standard for executive transparency and aligns with SEC best practices.
• The collar range (approx. 17% downside protection and 35% upside cap from current levels) is a standard conservative hedge for large concentrated positions.
• Retaining voting rights on pledged shares is a typical governance-friendly feature of executive loan facilities.

Corporate Governance

Related Party Transactions

• The transactions involve the Craig F. Courtemanche and Hillary Courtemanche Family Trust and the Courtemanche 2021 Irrevocable Trust.

Stakeholder Impact

• Shareholders: Minimal impact as the sales were pre-planned and the collar prevents immediate market dumping of 1.7 million shares.
• Management: The Chairman remains heavily incentivized with a multi-million share stake.

Next Steps

• Monitor for any further sales under the 10b5-1 plan in subsequent months.
• Observe if other insiders adopt similar collar strategies for liquidity.

Key Dates

Recommendation

The insider activity is structured and pre-planned, indicating routine personal financial management rather than a shift in corporate strategy or outlook. The Chairman's massive remaining stake suggests continued alignment with shareholders.

Keywords

Procore Technologies, PCOR, Insider Trading, Form 4, Craig Courtemanche, Stock Options, 10b5-1 Plan, Equity Collar, Share Pledge, Construction Software